RU2011150205A - Способ получения аминополиалкиленфосфоновых кислот - Google Patents
Способ получения аминополиалкиленфосфоновых кислот Download PDFInfo
- Publication number
- RU2011150205A RU2011150205A RU2011150205/04A RU2011150205A RU2011150205A RU 2011150205 A RU2011150205 A RU 2011150205A RU 2011150205/04 A RU2011150205/04 A RU 2011150205/04A RU 2011150205 A RU2011150205 A RU 2011150205A RU 2011150205 A RU2011150205 A RU 2011150205A
- Authority
- RU
- Russia
- Prior art keywords
- acid
- groups
- branched
- linear
- cyclic
- Prior art date
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- 150000003009 phosphonic acids Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004122 cyclic group Chemical group 0.000 claims abstract 21
- 238000000034 method Methods 0.000 claims abstract 19
- 150000001412 amines Chemical class 0.000 claims abstract 15
- 125000003118 aryl group Chemical group 0.000 claims abstract 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 9
- 239000002253 acid Substances 0.000 claims abstract 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 24
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 22
- 239000003377 acid catalyst Substances 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 9
- 239000003153 chemical reaction reagent Substances 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 239000012431 aqueous reaction media Substances 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 239000007795 chemical reaction product Substances 0.000 claims 4
- 238000004821 distillation Methods 0.000 claims 4
- 230000003993 interaction Effects 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- 239000007848 Bronsted acid Substances 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- 239000012429 reaction media Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229920002873 Polyethylenimine Polymers 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 1
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 claims 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 claims 1
- OEOOQMSPHMFXJL-UHFFFAOYSA-N 4-chlorobutan-1-amine Chemical compound NCCCCCl OEOOQMSPHMFXJL-UHFFFAOYSA-N 0.000 claims 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229960003767 alanine Drugs 0.000 claims 1
- 239000003513 alkali Chemical class 0.000 claims 1
- -1 alkaline earth metal cations Chemical class 0.000 claims 1
- 125000005262 alkoxyamine group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 229960002684 aminocaproic acid Drugs 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229940000635 beta-alanine Drugs 0.000 claims 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003729 cation exchange resin Substances 0.000 claims 1
- 229940023913 cation exchange resins Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 1
- 229960002989 glutamic acid Drugs 0.000 claims 1
- 239000002638 heterogeneous catalyst Substances 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000011081 inoculation Methods 0.000 claims 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
- 150000007517 lewis acids Chemical group 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 claims 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09161389.3 | 2009-05-28 | ||
| EP09161389 | 2009-05-28 | ||
| PCT/EP2010/057434 WO2010136573A1 (en) | 2009-05-28 | 2010-05-28 | Method for the manufacture of aminopolyalkylene phosphonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2011150205A true RU2011150205A (ru) | 2013-07-10 |
Family
ID=41264934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011150205/04A RU2011150205A (ru) | 2009-05-28 | 2010-05-28 | Способ получения аминополиалкиленфосфоновых кислот |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20130030204A1 (ja) |
| EP (1) | EP2435451A1 (ja) |
| JP (1) | JP2012528126A (ja) |
| CN (1) | CN102439017A (ja) |
| AU (1) | AU2010251896A1 (ja) |
| BR (1) | BRPI1012288A2 (ja) |
| CA (1) | CA2763761A1 (ja) |
| MX (1) | MX2011012588A (ja) |
| RU (1) | RU2011150205A (ja) |
| WO (1) | WO2010136573A1 (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103848865A (zh) * | 2012-12-04 | 2014-06-11 | 山东省泰和水处理有限公司 | 一种水处理剂氨基三亚甲基膦酸的连续化生产方法 |
| CN109046452B (zh) * | 2018-05-29 | 2022-02-08 | 南京大学 | 一种固载型杂多酸催化剂及其制备方法和应用 |
| CN111087423B (zh) * | 2019-12-19 | 2022-04-08 | 江苏姚氏环保技术有限公司 | 一种用黄磷制备氨基三亚甲基膦酸的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1681294A1 (en) * | 2005-01-17 | 2006-07-19 | Solutia Europe N.V./S.A. | Process for the manufacture of aminopolyalkylene-phosphonic acid compounds |
-
2010
- 2010-05-28 CA CA2763761A patent/CA2763761A1/en not_active Abandoned
- 2010-05-28 WO PCT/EP2010/057434 patent/WO2010136573A1/en active Application Filing
- 2010-05-28 CN CN2010800226309A patent/CN102439017A/zh active Pending
- 2010-05-28 US US13/322,676 patent/US20130030204A1/en not_active Abandoned
- 2010-05-28 RU RU2011150205/04A patent/RU2011150205A/ru unknown
- 2010-05-28 AU AU2010251896A patent/AU2010251896A1/en not_active Abandoned
- 2010-05-28 BR BRPI1012288A patent/BRPI1012288A2/pt not_active IP Right Cessation
- 2010-05-28 EP EP10724395A patent/EP2435451A1/en not_active Withdrawn
- 2010-05-28 MX MX2011012588A patent/MX2011012588A/es not_active Application Discontinuation
- 2010-05-28 JP JP2012512395A patent/JP2012528126A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN102439017A (zh) | 2012-05-02 |
| JP2012528126A (ja) | 2012-11-12 |
| BRPI1012288A2 (pt) | 2017-03-21 |
| CA2763761A1 (en) | 2010-12-02 |
| MX2011012588A (es) | 2012-04-11 |
| US20130030204A1 (en) | 2013-01-31 |
| EP2435451A1 (en) | 2012-04-04 |
| WO2010136573A1 (en) | 2010-12-02 |
| AU2010251896A1 (en) | 2011-11-17 |
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